Diethyl Ether → HCID 59371291, compound

HRID 2095415Notes

Reaction equation

HRID 2095415 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][CH2:15][CH2:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:24]=[N:25][CH:26]=[C:27]([O:29][CH2:30][C@H:31]3[CH2:35][CH2:34][CH2:33][N:32]3[C:36](OC(C)(C)C)=O)[CH:28]=2)[CH2:19][CH2:18]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[O-]S([O-])(=O)=O.[Na+].[Na+].CCOCC>C1COCC1.O>[CH2:7]([O:14][CH2:15][CH2:16][CH:17]1[CH2:18][CH2:19][N:20]([C:23]2[CH:24]=[N:25][CH:26]=[C:27]([O:29][CH2:30][C@H:31]3[CH2:35][CH2:34][CH2:33][N:32]3[CH3:36])[CH:28]=2)[CH2:21][CH2:22]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 59371411HCID 59371411, compound

Product 1

HCID 59371291HCID 59371291, compoundYield 111.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (46.4 mg, 1.22 mmol, 5 equiv.) in THF (2 mL) was added a solution of 3-[4-[2-(benzyloxy)ethyl]-1-piperidinyl]-5-[[1-(tert-butoxycarbonyl)-2(R)-pyrrolidinyl]methoxy]pyridine (121 mg, 0.24 mmol) in THF (0.5 mL). The resulting mixture was refluxed for 1.5 h, then cooled to room temperature. To a flask containing 4-5 g of Na2SO4 was added with stirring 40-50 mL of Et2O followed by the cooled reaction mixture. Water was subsequently added dropwise to quench the reaction. When no more gas was generated, the mixture was filtered, and the solid phase was washed with CH2Cl2/MeOH 4:1 (100-150 mL). Solvent removal furnished crude 3-[4-[2-(benzyloxy)ethyl]-1-piperidinyl]-5-[(1-methyl-2(R)-pyrrolidinyl)methoxy]pyridine (110 mg), which could be used in the following step without purification.

Workup

  1. temperatureThe resulting mixture was refluxed for 1.5 h
  2. additionwas added
  3. customfollowed by the cooled reaction mixture
  4. customto quench
  5. customthe reaction
  6. filtrationthe mixture was filtered
  7. washthe solid phase was washed with CH2Cl2/MeOH 4:1 (100-150 mL)
  8. customSolvent removal

Sources & evidence

ORD record
ord-730f3f2847d345f796b18820428bc1ee
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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